Triethylamine → 1-Benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate

HRID 1291117ノート

反応式

HRID 1291117 の反応式
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH2:27]([N:34]1[CH2:39][CH2:38][CH:37](O)[CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:37]2[CH2:36][CH2:35][N:34]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:39][CH2:38]2)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

参加物

5

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 784611-Benzylpiperidin-4-olHCID 189198834-Iodo-2-nitrobenzoic acid

生成物 1

HCID 189197541-Benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate収率 13%

実験手順

2.33 g (0.00795 mol) of 4-iodo-2-nitrobenzoic acid were boiled und reflux in 13.8 ml (0.16 mol) of oxalyl chloride for 3 hrs. After removal of the excess oxalyl chloride the mixture was concentrated twice with 30 ml of toluene each time. The residue was dissolved in 80 ml of toluene, treated with 1.94 ml (0.0139 mol) of triethylamine and 1.52 g (0.00795 mol) of 1-benzyl-4-hydroxypiperidine and boiled at reflux for 18 hrs. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:3). 0.465 g (13%) of 1-benzyl-piperidin-4-yl 4-iodo-2-nitrobenzoate was obtained as a yellow oil. MS: me/e=467 (C19H20IN2O4 +).

後処理

  1. customAfter removal of the excess oxalyl chloride the mixture
  2. concentrationwas concentrated twice with 30 ml of toluene each time
  3. dissolutionThe residue was dissolved in 80 ml of toluene
  4. temperatureat reflux for 18 hrs
  5. customAfter removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane (1:3)

出典と根拠

ORDレコード
ord-805d4621af5a4fdeb907d30afc524839
出典データセット
uspto-grants-1998_05
特許番号
US05753679

反応ノート

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